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Additional compounds within the scope of this invention may be prepared using the methods illustrated in these Examples, either alone or in combination with techniques generally known in the art.Experiments were generally carried out under inert atmosphere (nitrogen or argon), particularly in cases where oxygen- or moisture-sensitive reagents or intermediates were employed. Yield: 150 mg, 0.598 mmol, 63%. . A mixture of C23 (120 mg, 0.467 mmol), C28 (105 mg, 0.469 mmol), tris(dibenzylideneacetone)dipalladium(0) (12.8 mg, 14.0 μmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos; 17.8 mg, 30.8 μmol), and cesium carbonate (608 mg, 1.87 mmol) in 1,4-dioxane (5 mL) was stirred at 100° C. for 16 hours.
In general, the solvated forms are considered equivalent to the unsolvated forms for the purposes of the present invention.The compounds of the invention may exist as clathrates or other complexes (e.g., co-crystals). The residue was combined with material from a similar reaction carried out using C3 (100 mg, 0.25 mmol) and purified via silica gel chromatography (Eluent: 1:1 ethyl acetate/petroleum ether). . The second type is the racemic mixture or conglomerate wherein two forms of crystal are produced in equimolar amounts each comprising a single enantiomer.The compounds of the present invention may also exist as an N-oxide thereof, or a pharmaceutically acceptable salt of the compound or N-oxide.As it is known to the person skilled in the art, amine compounds (i.e., those comprising one or more nitrogen atoms), for example tertiary amines, can form N-oxides (also known as amine oxides or amine N-oxides). A mixture of P2 (100 mg, 0.400 mmol), C27 (90.8 mg, 0.400 mmol), and 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine (167 mg, 1.20 mmol) in N,N-dimethylformamide (5 mL) was stirred at 85° C. for 16 hours. The mesomorphic state is intermediate between the true crystalline state and the true liquid state (either melt or solution).

Blister packs generally consist of a sheet of relatively stiff material covered with a foil of a transparent plastic material. From analysis of the A solution of C12 (400 mg, 1.31 mmol) in methanol (8 mL) was treated with hydrogen chloride (4 M solution in methanol; 4.0 mL, 16 mmol), and the reaction mixture was stirred at room temperature (20° C.) for 15 hours. After addition of hydrochloric acid (1 M; 20 mL) and removal of solvents in vacuo, the residue was taken up in acetonitrile (50 mL) and filtered through diatomaceous earth. After the reaction mixture had been concentrated in vacuo, the residue was purified via silica gel chromatography (Gradient: 0% to 15% methanol in dichloromethane) to afford the product as a solid. Referring to Scheme 7, a compound of Formula 6-3, wherein PGScheme 8 refers to preparation of a compound of Formula 8-5, wherein RScheme 9 refers to preparation of a compound of Formula 9-3, wherein RAdditional starting materials and intermediates useful for making the compounds of the present invention can be obtained from chemical vendors such as Sigma-Aldrich or can be made according to methods described in the chemical art.Those skilled in the art can recognize that in all of the Schemes described herein, if there are functional (reactive) groups present on a part of the compound structure such as a substituent group, for example RSimilarly, those skilled in the art can also recognize that in all of the schemes described herein, if there are functional (reactive) groups present on a substituent group such as RAs used herein, the term “reacting” (or “reaction” or “reacted”) refers to the bringing together of designated chemical reactants such that a chemical transformation takes place generating a compound different from any initially introduced into the system. Concentration of the eluate affords the enriched mixture. When present in racemic compounds, solid and dotted wedges are used to define relative stereochemistry, rather than absolute stereochemistry. The residue was subjected to reversed-phase HPLC (Column: Waters XBridge C18 OBD, 5 μm; Mobile phase A: water containing 0.05% ammonium hydroxide; Mobile phase B: acetonitrile; Gradient: 22% to 52% B) to provide the product as a white solid. Yield: 249 mg, 1.66 mmol, 52%. The reaction mixture was then poured into water (10 mL) and extracted with ethyl acetate (3×10 mL). al., “M1 and M4 Receptors Modulate Hippocampal Pyramidal Neurons”, J. Neurophysiology 105: 779-792, 2011) through modulation of the hippocampal trisynaptic pathway which has been reported to be disregulated in Schizophrenic (Tamminga, Carol A., et. The compound according to claim 1 that is 1-{4-[(cyclopropylmethyl)amino]-6,7-dimethyl-1,3-dihydro-2H-pyrrolo[3,4-c]pyridin-2-yl}-2-[1-(pyrimidin-4-yl)azetidin-3-yl]ethanone, or an N-oxide thereof, or a pharmaceutically acceptable salt thereof, or a pharmaceutically acceptable salt of the N-oxide.22.

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